2- Phenylethyl methyl sulfide

Jorgenson (282) isolated the following substances from red fox urine isopentenyl methyl sulfide (60), 2-phenylethyl methyl sulfide (61), 6-methyl-5-hepten-2-one (62) and /ra -geranylacetone (63) from both sexes and additionally 2-methylquinoline (64) from urine of males. 

In the oxidation of aryl methyl sulfides catalyzed by chloroperoxidase from Caldariomyces fumago with racemic 1-phenylethyl hydroperoxide instead of H2O2 as oxygen donor, it was found that (k)-sulfoxides, the (S)-hydroperoxides and the corresponding (k)-alcohol are produced in moderate to good enantiomeric excesses by double stereodifferentiation of the substrate and oxidant (Eq. 2, Table 3) [68]. 

Organic compounds normally cause Htde or no corrosion of magnesium. Tanks or other containers of magnesium alloys are used for phenol [108-95-2] methyl bromide [74-96 ] and phenylethyl alcohol [60-12-8]. Most alcohols cause no more than mild attack, but anhydrous methanol attacks magnesium vigorously with the formation of magnesium methoxide [109-88-6]. This attack is inhibited by the addition of 1% ammonium sulfide [12135-76-1] or the presence ofwater. 

Hoft reported about the kinetic resolution of THPO (16b) by acylation catalyzed by different lipases (equation 12) °. Using lipases from Pseudomonas fluorescens, only low ee values were obtained even at high conversions of the hydroperoxide (best result after 96 hours with lipase PS conversion of 83% and ee of 37%). Better results were achieved by the same authors using pancreatin as a catalyst. With this lipase an ee of 96% could be obtained but only at high conversions (85%), so that the enantiomerically enriched (5 )-16b was isolated in poor yields (<20%). Unfortunately, this procedure was limited to secondary hydroperoxides. With tertiary 1-methyl-1-phenylpropyl hydroperoxide (17a) or 1-cyclohexyl-1-phenylethyl hydroperoxide (17b) no reaction was observed. The kinetic resolution of racemic hydroperoxides can also be achieved by chloroperoxidase (CPO) or Coprinus peroxidase (CiP) catalyzed enantioselective sulfoxidation of prochiral sulfides 22 with a racemic mixmre of chiral hydroperoxides. In 1992, Wong and coworkers and later Hoft and coworkers in 1995 ° investigated the CPO-catalyzed sulfoxidation with several chiral racemic hydroperoxides while the CiP-catalyzed kinetic resolution of phenylethyl hydroperoxide 16a was reported by Adam and coworkers (equation 13). The results are summarized in Table 4. 

A further catalytic method for asymmetric sulfoxidation of aryl alkyl sulfides was reported by Adam s group, who utilized secondary hydroperoxides 16a, 161 and 191b as oxidants and asymmetric inductors (Scheme 114) . This titanium-catalyzed oxidation reaction by (S)-l-phenylethyl hydroperoxide 16a at —20°C in CCI4 afforded good to high enantiomeric excesses for methyl phenyl and p-tolyl alkyl sulfides ee up to 80%). Detailed mechanistic studies showed that the enantioselectivity of the sulfide oxidation results from a combination of a rather low asymmetric induction in the sulfoxidation ee <20%) followed by a kinetic resolution of the sulfoxide by further oxidation to the sulfone... 

The best results were obtained with (S)-(-)-phenylethyl hydroperoxide 47 at -20 °C in CC14, which afforded (S)-sulfoxides with low to modest enantioselectivity and low yield. A time profile of the oxidation of methyl p-tolyl sulfide with 47 showed that the asymmetric induction in the sulfoxidation was rather low (< 20%), demonstrating that the enantioselectivity obtained is related to a concomitant kinetic resolution of the sulfoxide formed. 

Triorgano telluronium salts may lose an organic group to form diorgano tellurium compounds. This reductive elimination is influenced by the nature of the organic groups and the nature of the anion. Methyl" ", benzyl and 2-oxo-2-phenylethyl groups" are especially easy to cleave. However, loss of phenyl iodide was observed when triphenyl telluronium iodide was heated with sodium sulfide nonahydrate . 

Lambert and Goethals attempted to prepare block copolymers of tetrahydrofuran (THF) with propylene sulfide, thiethane, 3,3-dimethylthiethane, aziridine and l-(2-phenylethyl)-2-methyl-aziridine123). None of these systems gave pure block copolymers. Except with aziridine, mixtures of block copolymers and polyTHF was found from solubility data. With unsubstituted aziridine transfer led to a mixture of homopolymers ... 

Camembert-type cheeses with a powdery rind of white mold Penkillium camemberti) smeU pleasantly of mushrooms, earth and garlic. The characteristic component of the mushroom-like odour is oct-l-en-3-ol, the floral odour components are primarily 2-phenylethanol and 2-phenylethyl acetate, and 1,3-dimethoxybenzene and methyl cinnamate are responsible for the odour resembling nuts. The garlic note of matured cheese is caused by the presence of sulfur compounds, such as 2-bis (methylthio)methane, also known as bis(dimethylsulfanyl)-methane or 2,4-dithiapentane, tris(methylthio) methane, also known as tris(methylsulfanyl)methane or 3-methylthio-2,4-dithiapentane, methyl (methylthio)methyl disulfide, also known as (methyldisuflanyl) methylsulfanylmethane or 2,3,5-trithiahexane, and bis(methylthiomethyl) sulfide (8-186). 

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